Premium
(−)‐Daucic Acid: Revision of Configuration, Synthesis, and Biosynthetic Implications
Author(s) -
Lichtenthaler Frieder W.,
Nakamura Katsumi,
Klotz Jürgen
Publication year - 2003
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200352718
Subject(s) - stereochemistry , galactose , carbon atom , mannose , chemistry , biosynthesis , biochemistry , organic chemistry , gene , ring (chemistry)
The synthesis of dihydropyrans with the D ‐ xylo ( 1 ), D ‐ ribo , L ‐ arabino , and D ‐ lyxo ( 2 ) configuration by one‐carbon‐atom homologation of D ‐mannose or D ‐galactose, terminal oxidation, and directed β elimination revealed (−)‐daucic acid isolated from carrots to be 2 , rather than 1 as previously thought. The identical configuration of 2 and KDO 8‐P ( 3 ) and available biosynthetic information about chelidonic acid ( 4 ) suggest a KDO 8‐P based pathway for the generation of 2 and 4 in plants.